Just being pedantic here, but: if we take your approach to the extreme, we would only ever pick the one thing that maximizes joy. Eg say one week trips above are the coolest thing you can think of. then you'd compare any potential purchase against it, and it would fall short. So you'd end upmnever buying anything (except tickets for one week trips). Don't get me wrong, your strategy sounds sound, I'm just saying that it's too greedy of an algorithm to apply it thoroughly. A slightly improved strategy would be to instead think of marginal prices: how much would I be willing to pay for X, instead of another piece of Y. Ie, if you already had 10 one week trips this year, you'd not be willing to spend as much for #11 than you'd be willing to spend to go from from 0 to 1 trips or 1 to 2